Players like Drew and Varitek are just getting too old I'm afraid. I don't dislike Drew, he just can't stay healthy any more. Tek is the Captain! But he struggled at the plate and really can't throw anyone out stealing anymore.
Lackey is just a big crybaby. Making faces when his teammates don't make plays, whatever he did to his wife. He's a loser.
Crawford? Sorry dude, you have to put up after coming over from a Division rival and signing that huge contract. And the way he performed in left field in the last few games...heck, might as well have Alfonso Soriano out there. At least he'll hit.
Now, are these horrible contracts by Epstein? Look at every team in the league. Certain guys are getting ridiculous contracts. Huge numbers and way too many years. If the player performs, then it's a good contract. If the player tanks, then it's a bad contract.
Take ARod for example. His contract in Texas was terrible for Texas. In New York, it's a great contract...well, depends on whether he's in the regular season or the post season!